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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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2,2-Dimethoxypropane → ((3aR,4R,6R,6aS)-6-(5-Iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

HRID 1507478
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HRID 1507478 반응식
[OH:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([NH:8][C:9]2[C:14]([I:15])=[C:13]([O:16][CH3:17])[N:12]=[C:11]([S:18][CH3:19])[N:10]=2)[C@H:5]([OH:20])[C@@H:4]1[OH:21].CO[C:24](OC)([CH3:26])[CH3:25].CCN(CC)CC>CC(C)=O.CS(O)(=O)=O>[I:15][C:14]1[C:9]([NH:8][C@H:6]2[C@@H:5]3[O:20][C:24]([CH3:26])([CH3:25])[O:21][C@@H:4]3[C@@H:3]([CH2:2][OH:1])[CH2:7]2)=[N:10][C:11]([S:18][CH3:19])=[N:12][C:13]=1[O:16][CH3:17]
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참가 물질

6

반응물 3

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 117677905(1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol

생성물 1

HCID 117677839((3aR,4R,6R,6aS)-6-(5-Iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

시약·촉매·용매 2

HCID 6395
Methanesulfonic Acid
촉매
HCID 180Acetone용매

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온도
0 °C

실험 절차

Compound 5 (4.00 g, 9.36 mmol) was dissolved in acetone (10 mL) and 2,2-dimethoxypropane (5.75 mL, 46.8 mmol) was added. The solution was cooled to 0° C. and methanesulfonic acid (2 drops) was added. The solution was stirred for 15 min and Et3N (1 mL) was added. The acetone was evaporated and the residue was dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography on silica gel (EtOAc/hexanes) to give the title compound as a white solid. 1H NMR (CDCl3) δ 6.21 (d, J=8 Hz, 1H), 4.65-4.59 (m, 2H), 4.45-4.44 (m, 1H), 3.94 (s, 3H), 3.89-3.85 (m, 1H), 3.76-3.73 (m, 1H), 2.61-2.55 (m, 1H), 2.52 (s, 3H), 2.40-2.34 (m, 1H), 1.85 (br s, 1H), 1.65-1.57 (m, 2H), 1.49 (s, 3H), 1.28 (s, 3H); LCMS 2.54 min, 468 (M+H).

후처리

  1. customThe acetone was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via column chromatography on silica gel (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-29b201806dd549258b9d8e9107ad2337
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221809B2

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